South Pasadena Homes with Gated Community - Guard Community Features

South Pasadena Homes with Gated Community - Guard Community Features

Welcome to South Pasadena, Florida, a hidden gem nestled in the heart of Pinellas County. This charming city boasts a unique blend of coastal beauty, vibrant community spirit, and convenient access to the best that the Sunshine State has to offer. With its lush landscapes and proximity to the sparkling waters of the Gulf of Mexico, South Pasadena is an ideal location for those seeking a tranquil lifestyle with the perks of urban living.

One of the standout features of South Pasadena is its selection of homes within gated communities, offering an exclusive and secure environment for residents. These guard-gated communities provide peace of mind, ensuring that you and your loved ones can enjoy your home in a safe and serene atmosphere. The meticulously maintained landscapes and elegant architecture of these neighborhoods create an inviting ambiance that enhances the overall living experience.

Residents of South Pasadena can take advantage of a plethora of nearby amenities, including beautiful parks, boutique shops, and delightful restaurants, all while being just a short drive away from the bustling city of St. Petersburg. The community is also known for its friendly atmosphere and active social scene, making it easy to forge connections with neighbors and enjoy a fulfilling lifestyle.

Whether you're looking for a cozy retreat or a spacious family home, South Pasadena's gated communities offer a variety of options tailored to your needs. Experience the perfect blend of comfort, security, and community in this picturesque Florida city—your dream home awaits!

Newest South Pasadena Homes with Gated Community - Guard Community Features

3 Beds ⋅ 2 Baths ⋅ Harbourside Condo SubDv. ⋅ 33707 Zip Code

Virtually Staged. Virtually Staged. Welcome to an extraordinary opportunity to own a slice of paradise at the prestigious Windwards at Harbourside Building 8, Penthouse Unit 804. This meticulously updated, 1,915 sq. ft. penthouse is a rare find, being one of only a few located on the island, offering unparalleled resort-style living in South Pasadena FL. Key Residence Features includes Luxurious Interiors: Step inside to a magnificent tiled floor featuring a centered marble compass, guiding you through this expansive residence with crown molding and plantation shutters on every window. The entire condo has been freshly painted in "White Cloud" to match the pristine flooring and countertops. Spacious Living: The flexible floor plan includes a large, Waterview 14x13 room perfect for a den or third bedroom, and a 28x14 living room that can be configured into distinct conversation and media areas. Gourmet Kitchen & Dining: The renovated kitchen boasts newer cabinets and appliances, multiple pantries, a dedicated laundry room with a sink, and a dining area offering stunning views of the Gulf and intracoastal waterway. Master Suite Retreat: The master bedroom features an ensuite bathroom with a luxurious Jacuzzi tub, separate shower, and powder room. Premium Upgrades: Enjoy peace of mind with two A/C units (master bedroom 2025 and kitchen 2026), a tankless water heater, a whole-house water filtration system (2023), new sliders and windows installed 2026, and hurricane shutters on the balcony, bedrooms and den. Abundant Storage & Parking: The unit includes a storage unit on the balcony and another large one on the same floor (#804). Two parking spaces are provided: under Building 134 and Car Port #89. Harbourside Amenities & Community: Harbourside is renowned for its solid steel-reinforced concrete construction and an extensive array of amenities that cater to a vibrant, active lifestyle: Pools & Fitness: Access to six swimming pools (including one specific to the Windward building plus the main clubhouse pool), two fitness centers, separate men's and women's gyms, Jacuzzi, saunas, and three car wash stations. Sports & Recreation: Three tennis courts, three pickleball courts, shuffleboard, and a 1.5-mile walking trail around the island, perfect for exercise or walking your pet (Windward Building allows one pet under 20 pounds) Hobbies & Social: Enjoy a woodworking shop, library, card room, billiard room, outdoor grilling areas, car charging stations, and a clubhouse with a full social agenda. Waterfront Living: The community features a marina with three docks and 87 deeded slips (slips are available to rent or purchase from other owners), and two kayak racks with 50 spaces each. Experience resort-style living at its finest in this magnificent penthouse. Close to downtown, shopping, medical and walking distance to the BEACH!

7932 Sailboat Key Boulevard S Unit 804, South Pasadena

1 Beds ⋅ 1 Baths ⋅ Savannah Condo SubDv. ⋅ 33707 Zip Code

Welcome to Harbourside, a premier waterfront community delivering the quintessential coastal lifestyle. This gorgeous ground-floor residence has been thoughtfully updated with updated stainless steel kitchen appliances and sleek modern light fixtures. Live with piece of mind and high and dry feeling as there was no water intrusion from 2024 hurricanes. Property Highlights: Generous Layout: Spacious 1-bedroom floor plan designed for maximum comfort and effortless living. Ground-Floor Ease: Enjoy hassle-free, stair-free access straight to your front door. Serene Water Views: Step out onto your expansive private balcony—the perfect backdrop for morning coffee, evening relaxation, or entertaining guests. Partially Furnished: Owner willing to leave some items with the right offer. Resort-Style Community Amenities: Take advantage of top-tier facilities including a sparkling swimming pool, a fully equipped fitness center, and lush, meticulously maintained grounds featuring scenic walking paths along the water. Prime Location: Situated just one mile from the Gulf's pristine sandy beaches, you are only minutes from sun, surf, local dining, and shopping. Whether you are seeking a primary residence, a seasonal getaway, or a high-value investment, this move-in-ready coastal retreat is a rare find. Schedule your private tour today and start living the waterfront dream! Buy with complete peace of mind! The Milestone Inspection is complete. No Assesments currently being discussed to Owners knowledge.

7903 Sailboat Key Boulevard S Unit 102, South Pasadena

4 Beds ⋅ 4 Baths ⋅ Skimmer Point Ph Ii SubDv. ⋅ 33707 Zip Code

Virtually Staged. AN EXCEPTIONAL POINT OF VIEW ON BOCA CIEGA BAY. Experience exceptional waterfront living in Pasadena Yacht & Country Club from this beautifully remodeled, single-story residence situated on a coveted point lot with approximately 174.5 feet of waterfront and sweeping open views toward Boca Ciega Bay. Designed for effortless Florida living and entertaining, the open-concept interior features dramatic volume ceilings reaching approximately 13 feet, abundant natural light, wide-plank luxury vinyl flooring throughout, designer lighting and a wood-burning fireplace. Significant improvements include a new roof, new hurricane-rated windows and doors, and a newer seawall. The flexible split-bedroom floor plan offers 3 bedrooms plus an office or optional 4th bedroom and 3.5 baths. The spacious primary suite is a private retreat with a walk-in closet and beautifully appointed bath featuring a soaking tub, walk-in shower and private water closet. Updates include hurricane windows and doors, newer roof (2020) newer seawall (2017), new artificial turf front yard and more! Outside, the point-lot setting takes center stage. Relax by the pool, entertain along the waterfront and enjoy expansive views across Boca Ciega Bay. The oversized 667 SF garage features new epoxy flooring and ample room for vehicles, storage and recreational gear and golf cart. Adding further distinction for a waterfront property, the home DID NOT FLOOD during Hurricane Helene. An exceptional benefit of purchasing within Pasadena Yacht & Country Club: buyers have the ability to bypass the golf membership waitlist and join as a Full Golf Member within 30 days of purchase, if they choose—offering the opportunity to enjoy the club lifestyle without the wait. Ideally located near vibrant Downtown St. Petersburg and minutes from St. Pete Beach and Florida's renowned Gulf beaches, this home places boating, golf, dining, arts, culture and the best of the St. Petersburg lifestyle within easy reach. Remodeled, refined and remarkably waterfront—this is Florida living from the fairway to the bay and the beach beyond.

5921 Seabird Drive S, Gulfport

2 Beds ⋅ 2 Baths ⋅ Bay Island Group 3 SubDv. ⋅ 33707 Zip Code

A solid waterfront opportunity in Bay Island - offering functional living in one of the area’s premier gated 55+ communities. Located in a 24-hour guarded neighborhood, this 2-bedroom, 2-bathroom residence offers a practical, comfortable layout featuring durable waterproof laminate flooring through the living, dining, and primary suite. The kitchen comes equipped with granite countertops, a double oven and a convenient pass-through to the dining area. Both bathrooms are appointed with granite-topped vanities, with the primary suite offering updated shaker-style cabinetry with excellent storage, a walk-in shower, and a dedicated walk-in closet in the bedroom. Everyday peace of mind is built in with impact windows throughout, offering insulated, storm-ready protection and clear views looking out toward the water. Living in Bay Island means you can enjoy an active, resort-style environment. Community amenities include multiple heated pools, waterfront tiki huts, grilling areas, tennis, pickleball, and shuffleboard courts, plus a waterfront walking path and a clubhouse with a fitness center and social activities. The monthly fee covers basic cable, high-speed internet, water, sewer, trash, flood insurance, exterior groundskeeping, and 24-hour security. Pet-friendly (up to 2 pets, 1 dog max under 15 lbs) with flexible rental guidelines (30-day minimum, 3x per year). A SunRunner transit stop sits right outside the gates for easy rides to nearby beaches and downtown St. Petersburg. Whether you're seeking an accessible price point in a premier waterfront enclave or an easy-living coastal retreat, this residence delivers outstanding value in an unbeatable location. Schedule your private tour today.

7465 Bay Island Drive S Unit 313, South Pasadena

1 Beds ⋅ 2 Baths ⋅ Bay Island Group 1 SubDv. ⋅ 33707 Zip Code

Beautiful 7th floor condo with views of Boca Ciega Bay from your spacious living room, dining room, and enclosed lanai/porch with tile floor. Large master suite provides a luxury feel with a large walk-in closet. This condo has been totally remodeled. The kitchen features new, shaker-style cabinets, granite countertops, butcher block island & stainless steel appliances. Luxury vinyl plank flooring throughout. Both bathrooms have been renovated. Amenities include a beautiful clubhouse, fitness center, sauna, tennis courts, swimming pools, hot tubs, shuffleboard, docks, and walking/jogging path encircling the complex. Convenient to shopping, medical complex, restaurants, and the sandy beaches of the Gulf of Mexico. If you are looking for your slice of paradise in a gated, waterfront, 55+ community, schedule your showing now!

7400 Sun Island Drive S Unit 709, South Pasadena

3 Beds ⋅ 2 Baths ⋅ Coral Pointe SubDv. ⋅ 33707 Zip Code

Virtually Staged. Wide-open views of Boca Ciega Bay and two private balconies set the stage for waterfront living in Coral Pointe at Harbourside, a gated resort-style community in St. Pete Beach. This light-filled end unit features a split-bedroom layout with two bedrooms, an office/den that may serve as a third bedroom, and two full baths. The expansive waterfront balcony is accessible from both the living room and primary suite, offering sunrise views across the bay, while a second west-facing balcony off the kitchen and office/den provides a separate place to enjoy evening sunsets. Multiple windows and sliding glass doors bring natural light and water views into the living and dining areas. The kitchen features ample, clean-lined cabinetry, stainless steel appliances, and a pass-through that keeps it connected to the living area. At the far end, the breakfast nook is wrapped in windows on three sides and opens to the west-facing balcony, creating an inviting setting for morning coffee, casual meals, and evening views. The primary suite opens directly to the waterfront balcony and includes a large walk-in closet. Its ensuite bath is divided into a separate vanity area and an enclosed section with the tub-shower combination and toilet. A second bedroom and nearby guest bath offer comfortable accommodations for family or visitors. Double folding doors open to the office/den, where sliding glass doors lead to the west-facing balcony, allowing the room to function as a home office, den, or additional sleeping accommodations. In-unit laundry and multiple closets add everyday convenience. Hurricane shutters and steel-reinforced concrete construction provide added peace of mind, along with a newer air-conditioning system and water heater installed in 2022 and stainless steel appliances added in 2023. Other notable features include assigned under-building parking space #71, plus additional under-building guest parking, a distinctive convenience found only in the Coral Pointe buildings. A large private storage unit near the elevator provides room for bicycles, beach gear, seasonal items, and household belongings. Harbourside complements its waterfront setting with an extensive collection of resort-style amenities. Six swimming pools, tennis and pickleball courts, fitness facilities, a Jacuzzi, saunas, shuffleboard, and grilling areas offer many ways to stay active or relax, while car-wash stations and electric-vehicle charging add convenience. The clubhouse features a full social calendar, library, card room, billiards room, and woodworking shop. Boaters can enjoy the private marina with three docks and 87 deeded slips, which may become available for rent or purchase from individual owners. A fishing pier, seawall, and 1.5-mile walking trail provide additional ways to enjoy the waterfront surroundings. Gulf beaches, dining, shopping, downtown St. Petersburg, arts, entertainment, and waterfront activities are all within convenient reach. Schedule your private tour today.

8001 Sailboat Key Boulevard S Unit 201, St Pete Beach

2 Beds ⋅ 2 Baths ⋅ Harbourside Condo SubDv. ⋅ 33707 Zip Code

This is a well maintained waterfront unit in Harbourside Condos in South Pasadena INCLUDING A DEEP WATER BOAT SLIP/LIFT (there are only 87 slips total for 800 units). It's a 16,000 lb Deco all aluminum and stainless steel cradle lift. Harbourside is a resort-like condo community on the intracoastal waterway 5 minutes from St Pete Beach. This unit's features are: HVAC system (2025), Stainless steel appliances, Hurricane shutters, Hurricane impact windows, 9' Ceilings and Dining and Living room combination with a Split Bedroom plan. The western view from the private balcony has beautiful Florida sunsets! The guest bedroom and kitchen also have beautiful water views. This desirable complex is guard gated (24 hour) with many amenities including 6 pools, his and hers fitness centers, shuffleboard, pickleball, tennis, hot tub, electric car charging stations, car wash stations, clubhouse with many social events throughout the year, library, card room, billiards room, arts and crafts room, wood working area, yoga and water exercise classes. There is a 1.5 mile walkway around the complex along the waterfront which is lit up for nightly walks. Come see what resort living in Florida is all about. You can live your tropical, island dream here in Harbourside.

7984 Sailboat Key Boulevard S Unit 303, St Petersburg

2 Beds ⋅ 2 Baths ⋅ Harbourside Condo SubDv. ⋅ 33707 Zip Code

****PRICE ADJUSTMENT**** LET'S GO! **** “BEACHWALKER” -Most desirable location in all of Harbourside— resort style living in one of South Pasadena’s finest waterfront communities. An immaculate, beautifully maintained, DIRECT WATERFRONT 2-bedroom 2- bath has been thoughtfully updated and cared for, providing comfort and quality. Plenty of natural daylight. West facing balcony with beautiful sunset views, enhanced by new gemstone floor coverings and protected with hurricane impact WINDOWS and electric shutters on both the balcony and primary bedroom— (shutter motor updated in 2023). Unit features newer stainless-steel appliances, updated ceiling fans and light fixtures, plantation shutters on all windows and the balcony, solid surface kitchen counters, and a granite vanity top in the primary bath. Additional upgrades include newer garbage disposal, kitchen faucet, and custom shelving in all closets. The AC (2019) and hot water tank (12/2022) ensure efficient, reliable performance. CONVENIENT UNDER BUILDING ASSIGNED PARKING SPACE #94. Complete Elevator modernization in 2025. A gated community with Exceptional amenities including Swimming pools and Spa's, EV charging stations, pickleball courts, tennis courts, shuffleboard, an active clubhouse, and miles of waterfront walking paths. Boat slips, guest boat docks (available on a first come-first serve) fishing pier, and a rare opportunity to own a pristine unit in a vibrant, amenity rich waterfront, community—perfect for full-time coastal living. Just minutes to the finest GULF Beaches. Oh, and a PET FRIENDLY community. Perfect timing to send out invites for the Pasadena Christmas boat parade that passes by right in front of your balcony. In addition, this unit is sold with a full wall media cabinet/bookcase with electric remote-control fireplace, plus a kitchen dinette table and 2 chairs. A MUST SEE! Schedule your showing.

7984 Sailboat Key Boulevard S Unit 306, South Pasadena

1 Beds ⋅ 2 Baths ⋅ Harbourside SubDv. ⋅ 33707 Zip Code

Virtually Staged. Welcome to resort style living in the community of Harbourside! From the moment of parking your car in the assigned end space just a few steps away from your ground floor entryway (no elevator aggravation), you’ll enter this well maintained and updated unit with an immediate view through the living room wall of window sliders and view of the lovely community green space and water. The kitchen with west facing hurricane impact window, shelved pantry, wood cabinetry and stone countertops is immediately available upon entry for ease of arranging your groceries. A storage room with HVAC (installed 6/26), water heater (2024) and laundry across the hall allows you to multi task if you wish. The guest bath, living room and bedroom walls have been updated with lovely shiplap. The dining room/living room combination with a wall of mirrors provides a comfortable space with engineered hardwood throughout and an end wall of hurricane impact sliders leading to the porch. A Murphy bed cabinet (no mattress included) can be utilized for those occasional guest visits or used as storage. The master bedroom is ample and can accommodate a king size bed with nightstands; the east facing wall has a hurricane slider looking out to the lanai and lovely landscaping, walking trail but can the window treatment provides heavy coverage for days of sleeping in. The master bath was uniquely updated with a walk in shower and the walk in closet styled with extra shelves for additional storage. The community has a marina for your vessel (slips are owned/leased by residents) and clubhouse providing something for everyone, from a library, 2 fitness centers, craft room, woodworking shop, gathering area, pool, spa, and tennis and pickleball courts, EV charging stations, car wash/vacuum & air. Enjoy the fresh air as you take a stroll or run around the community along the waterfront 1.5 mile trail. Safe and secure with 24/7 security manned gate. Conveniently located to nearby shopping and restaurants and just minutes to the Gulf beaches.

7897 Sailboat Key Boulevard Unit 107, South Pasadena

1 Beds ⋅ 1 Baths ⋅ Bay Island Group 14 SubDv. ⋅ 33707 Zip Code

Virtually Staged. PRICE IMPROVED !! ***HIGH and DRY - NO HURRICANE DAMAGE - NO WATER INTRUSION***SPECTACULAR LUXURY WATERFRONT CONDO with AMAZING DIRECT VIEWS of the BOCA CIEGA BAY*** Life is Great when you’re living in Paradise at the meticulously maintained Bay Island community. It’s a gated community with 24/7 security personnel. This gorgeous unit is located in the 8-story premier Presidential building. It’s a roomy 855 square feet of open plan with 1 Bedroom and 1 Full Bath. New LVP flooring was just installed throughout the condo. As a bonus…there is WASHER & DRYER laundry set inside the unit. Enjoy the sunsets and evening views of the Intracoastal waters from your private Balcony that's protected with a motorized HURRICANE SHUTTER for a high-level of protection. The timeless Kitchen was previously remodeled by prior ownership with solid-wood cabinets and beautiful countertops. The central HVAC system is only 1 year old. This unit comes with a dedicated Storage Closet big enough to store bicycles, beach chairs and small furniture. Your assigned covered parking spot is only a few steps away directly in front of the building’s entrance. Bay Island is a very active community for residents 55 years YOUNG or above. It boasts 6 heated swimming pools, 2 hot tubs, tennis and pickleball courts, shuffleboard, separate men and women fitness centers with locker rooms, a Clubhouse with party rooms, ping-pong tables, billiard tables, library and a full calendar of social events. There’s also an on-site MARINA for your boat - separately leased and subject to availability. The world-class Gulf Beaches of St Pete Beach, Treasure Island, Madeira Beach and Clearwater Beach are only minutes away and the famed Sunday Corey Ave Market is a stone’s throw across the iconic drawbridge. Come and enjoy the many beach bars with live bands or dine at the immense variety of restaurants that suit your taste. Downtown St. Petersburg is only a short drive where you can experience the many museums, theaters, parks, marinas, sidewalk dining, and cultural events – or come watch the Tampa Bay Rays play baseball and the Rowdies in a soccer match. Tampa International Airport (TPA) and the Clearwater-St Pete Airport (PIE) are about 30 minutes away. The MILESTONE INSPECTION REPORT and Structural Integrity Reserve Study are done. So come and enjoy life at this Waterfront Paradise with a Peace of Mind. Life is Good at Bay Island.

7600 Sun Island Drive S Unit 603, South Pasadena

2 Beds ⋅ 2 Baths ⋅ Bay Island Group 1 SubDv. ⋅ 33707 Zip Code

Wake up to paradise every single day! Tucked away in the premier, guard-gated 55+ active-lifestyle community of Bay Island, this beautifully renovated, turn-key 2BR/2BA waterfront oasis is ready for you to move right in. Positioned high and dry on the second floor, this immaculate home was completely unaffected by recent storms, offering ultimate peace of mind. Property Highlights: Perfect Exposure: East-facing orientation bathes the home in glorious morning light and gentle sunrises over Boca Ciega Bay, completely avoiding the intense afternoon heat. Serene Views: The expansive, screened lanai overlooks a peaceful, park-like waterfront setting—perfect for your morning coffee or evening relaxation. Spacious & Turn-Key: Fully furnished and exceptionally well-maintained, featuring 1,230 sq. ft. of comfortable living space with premium vinyl flooring and an abundance of storage, including a large primary walk-in closet. Resort-Style Amenities: Enjoy 24/7 guard-gated security, 6 heated pools, tennis and pickleball courts, a massive clubhouse, a fully equipped gym, and a marina. This pristine residence perfectly blends coastal relaxation with an active social calendar. Creative financing and flexible purchase solutions are welcomed. Schedule your tour today and start living the resort life!

7400 Sun Island Drive S Unit 203, South Pasadena

3 Beds ⋅ 2 Baths ⋅ Harbourside Condo SubDv. ⋅ 33707 Zip Code

Resort-Style Waterfront Living at Its Finest! Experience luxury coastal living in this beautifully updated 3-bedroom, 2-bath condominium offering approximately 1,300 square feet of elegant living space with breathtaking, unobstructed water views. From the moment you enter, you’ll appreciate the quality upgrades throughout, including high-impact windows and sliding glass doors, beautiful high-end laminate flooring, crown molding, chair rail accents, and Miami shutters. The spacious living and dining room combination provides the perfect setting for entertaining while taking in the spectacular waterfront scenery. The beautifully renovated kitchen features premium cabinetry, upgraded countertops, Frigidaire and GE stainless steel appliances, abundant cabinet storage, and a cozy breakfast nook. An inside laundry room with an LG stackable washer and dryer adds everyday convenience. The spacious primary suite offers stunning water views, private access to the rear balcony through impact sliding doors, a walk-in closet, and an updated bath with a walk-in shower. The guest bath also features a walk-in shower. The third bedroom, currently used as a home office, is complete with attractive French doors, making it a flexible space for work or guests. Enjoy true Florida living with two private balconies—one located just off the kitchen and a second expansive balcony accessible from both the living room and primary bedroom. The rear balcony features new tile flooring and panoramic water views. Storm shutters provide additional peace of mind on select windows, including both rear sliding doors. Additional features include ceiling fans throughout, under-building assigned parking, and abundant guest parking. The resort-style community offers an incredible list of amenities, including six swimming pools, pickleball courts, tennis courts, shuffleboard, electric vehicle charging stations, car wash stations, fitness center, and a beautifully renovated clubhouse featuring a library, card room, billiards room, and woodworking shop. Residents also enjoy yoga classes, water exercise programs, and a scenic 1.5-mile waterfront walking trail that winds throughout the community. Located just a short bike ride from some of Florida’s most beautiful beaches, popular waterfront restaurants, charming cafés, and lively beachside pubs, this exceptional condo offers the perfect combination of luxury, convenience, and the Florida lifestyle you’ve been dreaming of. Marina with several docks and many boat slips that are first-come first-serve. Some owners also offer available slips for rent. Come experience waterfront resort living every day!

7979 Sailboat Key Boulevard S Unit 101, South Pasadena

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